US4069054A
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Photopolymerizable composition containing a sensitized aromatic sulfonium compound and a cationacally polymerizable monomer
Assignee: 3M Co
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Filing: 1975-09-02
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Granted: 1978-01-17
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Expires: 1995-09-02
Abstract
Abstract Aromatic sulfonium compounds are sensitized to longer wavelengths of light by means of aromatic tertiary amines, aromatic tertiary diamines and certain aromatic polycyclic compounds.
Inventors
- 👤 George H. Smith
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 07:33
CPC Classifications
C; C08; C08F; C08F2/00; C08F2/46; C08F2/48; C08F2/50; G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/029; Y; Y10; Y10S; Y10S430/00; Y10S430/1053; Y10S430/1055; Y10S430/114; Y10S430/12; Y10S430/122
Claims Analysis
Total Claims: 4
Claim 1
Independent Claim
302 words
A photopolymerizable composition comprising: a. a cationically polymerizable monomer; b. an aromatic sulfonium compound of the following forumula: ##STR12## wherein R 1 , R 2 and R 3 are selected from the group consisting of aryl groups having 4 to 20 carbon atoms and alkyl radicals having 1 to 20 carbon atoms; wherein at least one of R 1 , R 2 and R 3 is aryl; wherein Z is selected from the group consisting of oxygen; sulfur; ##STR13## where R is aryl or acyl; a carbon-to-carbon bond; or ##STR14## where R 4 and R 5 are selected from the group consisting of hydrogen, an alkyl radical having 1 to 4 carbon atoms, and an alkenyl radical having 2 to 4 carbon atoms; and n is zero or 1; and X- is a halogen-containing complex anion selected from tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, and hexafluoroantimonate; and c. a sensitizing compound selected from the group consisting of: i. aromatic tertiary amines having the formula ##STR15## where Ar 1 , Ar 2 and Ar 3 are groups having 6-20 carbon atoms; Z is selected from oxygen; sulfur; ##STR16## a carbon-to-carbon bond; or ##STR17## where R 4 and R 5 are selected from hydrogen, alkyl radicals of 1-4 carbons, and alkenyl radicals of 2-4 carbons, and wherein n is zero or 1; ii. aromatic tertiary diamines having the formula ##STR18## where Y is a divalent radical selected from arylene and Ar 8 --Z--Ar 9 , where Z is as described above; Ar 4 , Ar 5 , Ar 6 , Ar 7 , Ar 8 and Ar 9 are aryl groups having 6-20 carbon atoms; and wherein n and m are zero or 1; and iii. aryl polycyclic compounds having at least three fused benzene rings and further having an ionization energy less than about 7.5 ev.
Claim 2
Dependent Claim
302 words
A photopolymerizable composition comprising: a. a cationically polymerizable monomer; b. an aromatic sulfonium compound of the following forumula: ##STR12## wherein R 1 , R 2 and R 3 are selected from the group consisting of aryl groups having 4 to 20 carbon atoms and alkyl radicals having 1 to 20 carbon atoms; wherein at least one of R 1 , R 2 and R 3 is aryl; wherein Z is selected from the group consisting of oxygen; sulfur; ##STR13## where R is aryl or acyl; a carbon-to-carbon bond; or ##STR14## where R 4 and R 5 are selected from the group consisting of hydrogen, an alkyl radical having 1 to 4 carbon atoms, and an alkenyl radical having 2 to 4 carbon atoms; and n is zero or 1; and X- is a halogen-containing complex anion selected from tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, and hexafluoroantimonate; and c. a sensitizing compound selected from the group consisting of: i. aromatic tertiary amines having the formula ##STR15## where Ar 1 , Ar 2 and Ar 3 are groups having 6-20 carbon atoms; Z is selected from oxygen; sulfur; ##STR16## a carbon-to-carbon bond; or ##STR17## where R 4 and R 5 are selected from hydrogen, alkyl radicals of 1-4 carbons, and alkenyl radicals of 2-4 carbons, and wherein n is zero or 1; ii. aromatic tertiary diamines having the formula ##STR18## where Y is a divalent radical selected from arylene and Ar 8 --Z--Ar 9 , where Z is as described above; Ar 4 , Ar 5 , Ar 6 , Ar 7 , Ar 8 and Ar 9 are aryl groups having 6-20 carbon atoms; and wherein n and m are zero or 1; and iii. aryl polycyclic compounds having at least three fused benzene rings and further having an ionization energy less than about 7.5 ev.
Claim 3
Dependent Claim
14 words
A photopolymerizable composition in accordance with claim 1, wherein said monomer is an epoxide.
Claim 4
Dependent Claim
21 words
A photopolymerizable composition in accordance with claim 1, wherein said sensitizing compound is selected from 2-ethyl-9,10-dimethoxyanthracene, anthracene, rubrene, tetraphenylbenzidine, and triphenylamine.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-01-16 | 1981-07-18 | 1982-01-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-16 | 1985-07-18 | 1986-01-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-16 | 1989-07-18 | 1990-01-17 | $7700.00 | Window Closed / Lapsed |